Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions

Ntakadzeni E. Madala, P. A. Steenkamp, L. A. Piater, I. A. Dubery

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


Nicotiana tabacum cell suspensions, 2 g wet wt/ml, rapidly took up 1 mM isonitrosoacetophenone (INAP), a plant-derived stress metabolite with anti-oxidative and anti-fungal properties, producing 4′-hexopyranosyloxy-3′-methoxyisonitrosoacetophenone in 54 % yield over 18 h. Unconverted INAP was at 33 μM. UPLC-MS/MS analyses with MassFragment software were used for metabolite identification. INAP had been hydroxylated at its meta- and para-positions as well as undergoing subsequent methoxylation and glycosylation. INAP is thus recognized by the enzymatic machinery of the phenylpropanoid pathway and is converted to a molecule with a substitution pattern similar to ferulic acid.

Original languageEnglish
Pages (from-to)1351-1356
Number of pages6
JournalBiotechnology Letters
Issue number7
Publication statusPublished - Jul 2012


  • 2-keto-2-phenyl-acetaldoxime
  • Biotransformation
  • Isonitrosoacetophenone
  • Metabolism
  • Nicotiana tabacum
  • Solanaceae
  • Xenobiotics

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology


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